TRANSFORMATION OF 5,6-DEHYDROKAWAIN AND TRANS-RESVERATROL WITH SELECTFLUORTM AND ACTIVITY TESTING ITS TRANSFORMATION AS AN ANTIBACTERIAL
5,6-Dehydrokawain (1) is a phenylpropanoid compound belonging to the cavalactone group contained in several species of the genera Alpinia and Piper methysticum. Compound 1 has been reported to have biological activity as anti-HIV, anticholesterol, antiobesity, antimicroba, antioxidant, anti-inflamma...
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| Format: | Theses |
| Language: | Indonesia |
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| Online Access: | https://digilib.itb.ac.id/gdl/view/68059 |
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| Institution: | Institut Teknologi Bandung |
| Language: | Indonesia |
| Summary: | 5,6-Dehydrokawain (1) is a phenylpropanoid compound belonging to the cavalactone group contained in several species of the genera Alpinia and Piper methysticum. Compound 1 has been reported to have biological activity as anti-HIV, anticholesterol, antiobesity, antimicroba, antioxidant, anti-inflammatory. Another phenylpropanoid compound that has a lot of activity is trans-resveratrol (2), this compound belongs to the stilbene group found in Venatrum grandiflorum, Poligonum cuspidatum, genus Eucalyptus, genus Picea, genus Vitis, and genus Arachis. The biological activities of compound 2 that have been reported are anticancer, antitumor, antiprolifetative, antiinflammatory, proapoptotic, neuroprotective, antiviral, anti-aging, antimicrobial, antidiabetic, antioxidant. For compound 1 it is necessary to carry out a fluorination reaction with acetonitrile and alcohol solvents which have two hydroxy groups (diol), ethylene glycol, thus allowing the formation of a compound product with an F group and a hydroxy group (-OH) so as to increase its biological activity and further modifications can be made. In addition, the transformation of trans-resveratrol compound with fluorination reaction has not been reported to compound 2. In carrying out the electrophilic fluorination reaction against the compounds 5,6-dehydrokawain (1) and trans-resveratrol (2), used reagent selectfluorTM (3) commercially available. This transformation is carried out through several stages, namely the reaction stage, fractionation and purification using VLC and RC techniques. Analysis of chromatography results was carried out by TLC. The compounds obtained were structurally determined by 1D NMR (1H, 13C, 19F, zTOCSY-1D), 2D NMR (HSQC and HMBC). In this research, three new compounds have been successfully transformed, (E)-3-fluoro-4-methoxy-6-styryl-2H-pyran-2-one (4) (6.0 %), 2-hydroxyethyl (E)- 2,2-difluoro-2-(2-(2-oxo-4-phenylbut-3-en-1-yl)-1,3-dioxolan-2-yl)acetate (5) (6.5 %), and (E)-4,6-difluoro-5-(4-hydroxystyryl)benzen-1,3-diol (6) (13.6 %). Based on the results of the activity as an antibacterial, Bacillus subtilis and Salmonella typhi bacteria. The transformed compound had better antibacterial activity than the precursor compound (except compound 5 against Salmonella typhi bacteria). |
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